504441-11-6

Upstream product

• 1461-22-9 tributyltin chloride 
• 65016-62-8 3-octylthiophene 

Downstream Products

• 1289493-08-8 5,5'-bis(4-octyl-5-(N,N-diphenyl-4-aminophenyl)-thiophen-2-yl)-2,2'-bipyridine 
• 1283598-33-3 1,4-bis(4-octyl-2-thienyl)-2,3-difluoro-5,6-dinitrobenzene 

Relevant academic research and scientific papers

Synthesis and characterization of new D-π-A and A-π-D-π-A type oligothiophene derivatives

In this work, we present a series of newly synthesized conjugated oligothiophene derivatives, with different numbers of central thiophene units, and different donor/acceptor architectures. Electrochemical and spectroscopic data have also been reported. We used thiophene or bithiophene as central donor core units, 3-octylthiophenes as π-bridge and solubilizing sub-units, and ethyl cyanoacetate or rhodanine moieties as acceptor end groups, in order to get D-π-A and A-π-D-π-A molecular architectures. The length of the synthesized oligothiophenes ranges from three to eight thiophene units, a variety that is sufficient to put in evidence different optical and electrochemical characteristics as well as semiconducting characteristics. Oligothiophene compounds can be regarded not only as models for the study of structure-property relationships relative to polythiophenes, but also they present a large number of applications in the field of organic electronics (i.e.: as donors in bulk-heterojunction solar cells and hole-transporting layer materials in perovskite solar cells, among others).

Highly fluorescent triazolopyridine-thiophene D-A-D oligomers for efficient pH sensing both in solution and in the solid state

Conjugated fluorophores have been extensively used for fluorescence sensing of various substances in the field of life processes and environmental science, due to their noninvasiveness, sensitivity, simplicity and rapidity. Most existing conjugated fluorophores exhibit excellent light-emitting performance in dilute solutions, but their properties substantially decrease or even completely vanish due to severe aggregation quenching in the solid state. Herein, we synthesize a series of triazolopyridine-thiophene donor-acceptor-donor (D-A-D) type conjugated molecules with high absolute fluorescence quantum yields (ΦF) ranging from 80% to 89% in solution. These molecules also show unusual light-emitting properties in the solid state with ΦF of up to 26%. We find that owing to the protonation-deprotonation process of the pyridine ring, these compounds display obvious changes in both fluorescence wavelength and intensity upon addition of acids, and these changes can be readily recovered by the successive introduction of bases. By harnessing this phenomenon, we further show that these fluorophores can be employed for efficient and reversible fluorescence sensing of hydrogen ions in a broad pH range (0.0-7.0). With the fabrication of pH testing papers and ink-printed complex patterns including butterflies and letters on substrates, we demonstrate the application of such sensors to fluorescence indication or solid state pH detection for real samples such as volatile acidic/basic gas and water-quality analysis.

Fluorenyl donor-acceptor H type molecular material with high fluorescence quantum efficiency and preparation method and applications thereof

The invention discloses a fluorenyl donor-acceptor H type molecular material with high fluorescence quantum efficiency and a preparation method and applications thereof. The bridging electron acceptor unit of Friedel-Crafts reactions of tertiary alcohol of a halogenated aryl group is taken as the bridging group; the aryl group is coupled to a chromophoric group through the halogen to form the H type molecular material, the structural formula of the molecular material is shown in the description, in the structural formula, Ar1, Ar2, Ar3, Ar4, and Ar11 individually represent an aryl group, Ar11 is an electron acceptor unit, Ar5, Ar6, Ar7, Ar8, Ar9, and Ar10 individually represent an aryl group or a non-aryl group; and SG1, SG2, SG3, and SG4 represent an aryl group or a non-aryl group. The synthesis of the material is in a modularization mode, the selection range of electron acceptor units is wide, the reaction steps are simple, the conditions are mild, and moreover, the molecular material has high thermal stability, electrochemical stability, and optical stability, and is an organic optoelectronic functional material with a wide application prospect.

Tuning the Solid State Emission of Thin Films/Microspheres Obtained from Alternating Oligo(3-octylthiophenes) and 2,6-Bis(pyrazole)pyridine Copolymers by Varying Conjugation Length and Eu3+/Tb3+ Metal Coordination

A series of dialkynyl-functionalized oligo(3-octylthiophene)m (m = 1-7 and 9, where m is the number of thiophene units) were polymerized together with 2,6-bis(pyrazole)pyridine (BPP) to get alternating copolymers (P1-P7 and P9) with the number-average molecular weights (Mn) in the range of 5.3-11 kDa. These copolymers were further self-assembled into solid microspheres. The optical emission range of these copolymers were fine-tuned from blue to red and white by changing the conjugation length of thiophene oligomers (band gap approximately from 2.1 to 1.67 eV) and coordination of metals like Eu3+ and Tb3+ in both the solution and solid states. A white color was obtained in solution, thin film, and microsphere states with CIE (Commission Internationale de l'Eclairage) coordinates close to the values of standard white color.

Synthesis and photovoltaic properties of alternating conjugated polymers derived from thiophene-benzothiadiazole block and fluorene/indenofluorene units

A new donor-accepter-donor-accepter-donor (D-A-D-A-D) type 2,1,3-benzothiadiazole-thiophene-based acceptor unit 2,5-di(4-(5-bromo-4- octylthiophen-2-yl)-2,1,3-benzothiadiazol-7-yl)thiophene (DTBTTBr2) wassynthesized. Copolymerized with fluorene and indeno[1,2-b]fluorene electron-rich moieties, two alternating narrow band gap (NBG) copolymers PF-DTBTT and PIF-DTBTT were prepared. And two copolymers exhibit broad and strong absorption in the range of 300-700 nm with optical band gap of about 1.75 eV. The highest occupied molecular orbital (HOMO) energy levels vary between -5.43 and -5.52 eV and the lowest unoccupied molecular orbital (LUMO) energy levels range from -3.64 to -3.77 eV. Potential applications of the copolymers as electron donor material and PC71BM ([6,6]-phenyl-C71 butyric acid methyl ester) as electron acceptors were investigated for photovoltaic solar cells (PSCs). Photovoltaic performances based on the blend of PF-DTBTT/PC71BM (w:w; 1:2) and PIF-DTBTT/PC71BM (w:w; 1:2) with devices configuration as ITO/ PEDOT: PSS/blend/Ca/Al, show an incident photon-to-current conversion efficiency (IPCE) of 2.34% and 2.56% with the open circuit voltage (Voc) of 0.87 V and 0.90 V, short circuit current density (Jsc) of 6.02 mA/ cm2 and 6.12 mA/cm2 under an AM1.5 simulator (100 mW/cm 2). The photocurrent responses exhibit the onset wavelength extending up to 720 nm. These results indicate that the resulted narrow band gap copolymers are viable electron donor materials for polymer solar cells.